High yield synthesis of high specific activity R-(-)-[11C]epinephrine for routine PET studies in humans

Pulak K. Chakraborty; David L. Gildersleeve; Douglas M. Jewett; Steve A. Toorongian; Michael R. Kilbourn; Markus Schwaiger; Donald M. Wieland

doi:10.1016/0969-8051(93)90094-B

High yield synthesis of high specific activity R-(-)-[¹¹C]epinephrine for routine PET studies in humans

Pulak K. Chakraborty
, David L. Gildersleeve
, Douglas M. Jewett
, Steve A. Toorongian
, Michael R. Kilbourn
, Markus Schwaiger
, Donald M. Wieland

University of Michigan Medical School

Research output: Contribution to journal › Article › peer-review

52 Scopus citations

Abstract

R-(-)-[¹¹C]Epinephrine ([¹¹C]EPI) has been synthesized from R-(-)-norepinephrine by direct methylation with [¹¹C]methyl iodide or [¹¹C]methyl triflate. The total synthesis time including HPLC purification was 35-40 min. The radiochemical yields (EOB) were 5-10% for [¹¹C]methyl iodide and 15-25% for [¹¹C]methyl triflate. Radiochemical purity was >98%; optical purity determined by radio-chiral HPLC was >97%. The [¹¹C]methyl triflate technique produces R-(-)-[¹¹C]epinephrine in quantities (80-170 mCi) sufficient for multiple positron emission tomography studies in humans. The two synthetic methods are generally applicable to the production of other N-[¹¹C]methyl phenolamines and N-[¹¹C]methyl catecholamines.

Original language	English
Pages (from-to)	939-944
Number of pages	6
Journal	Nuclear Medicine and Biology
Volume	20
Issue number	8
DOIs	https://doi.org/10.1016/0969-8051(93)90094-B
State	Published - Nov 1993
Externally published	Yes

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SDG 3 Good Health and Well-being

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10.1016/0969-8051(93)90094-B

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@article{80b373a15c344f1b93b83cc9b260c685,

title = "High yield synthesis of high specific activity R-(-)-[11C]epinephrine for routine PET studies in humans",

abstract = "R-(-)-[11C]Epinephrine ([11C]EPI) has been synthesized from R-(-)-norepinephrine by direct methylation with [11C]methyl iodide or [11C]methyl triflate. The total synthesis time including HPLC purification was 35-40 min. The radiochemical yields (EOB) were 5-10\% for [11C]methyl iodide and 15-25\% for [11C]methyl triflate. Radiochemical purity was >98\%; optical purity determined by radio-chiral HPLC was >97\%. The [11C]methyl triflate technique produces R-(-)-[11C]epinephrine in quantities (80-170 mCi) sufficient for multiple positron emission tomography studies in humans. The two synthetic methods are generally applicable to the production of other N-[11C]methyl phenolamines and N-[11C]methyl catecholamines.",

author = "Chakraborty, \{Pulak K.\} and Gildersleeve, \{David L.\} and Jewett, \{Douglas M.\} and Toorongian, \{Steve A.\} and Kilbourn, \{Michael R.\} and Markus Schwaiger and Wieland, \{Donald M.\}",

year = "1993",

month = nov,

doi = "10.1016/0969-8051(93)90094-B",

language = "English",

volume = "20",

pages = "939--944",

journal = "Nuclear Medicine and Biology",

issn = "0969-8051",

publisher = "Elsevier Inc.",

number = "8",

}

TY - JOUR

T1 - High yield synthesis of high specific activity R-(-)-[11C]epinephrine for routine PET studies in humans

AU - Chakraborty, Pulak K.

AU - Gildersleeve, David L.

AU - Jewett, Douglas M.

AU - Toorongian, Steve A.

AU - Kilbourn, Michael R.

AU - Schwaiger, Markus

AU - Wieland, Donald M.

PY - 1993/11

Y1 - 1993/11

N2 - R-(-)-[11C]Epinephrine ([11C]EPI) has been synthesized from R-(-)-norepinephrine by direct methylation with [11C]methyl iodide or [11C]methyl triflate. The total synthesis time including HPLC purification was 35-40 min. The radiochemical yields (EOB) were 5-10% for [11C]methyl iodide and 15-25% for [11C]methyl triflate. Radiochemical purity was >98%; optical purity determined by radio-chiral HPLC was >97%. The [11C]methyl triflate technique produces R-(-)-[11C]epinephrine in quantities (80-170 mCi) sufficient for multiple positron emission tomography studies in humans. The two synthetic methods are generally applicable to the production of other N-[11C]methyl phenolamines and N-[11C]methyl catecholamines.

AB - R-(-)-[11C]Epinephrine ([11C]EPI) has been synthesized from R-(-)-norepinephrine by direct methylation with [11C]methyl iodide or [11C]methyl triflate. The total synthesis time including HPLC purification was 35-40 min. The radiochemical yields (EOB) were 5-10% for [11C]methyl iodide and 15-25% for [11C]methyl triflate. Radiochemical purity was >98%; optical purity determined by radio-chiral HPLC was >97%. The [11C]methyl triflate technique produces R-(-)-[11C]epinephrine in quantities (80-170 mCi) sufficient for multiple positron emission tomography studies in humans. The two synthetic methods are generally applicable to the production of other N-[11C]methyl phenolamines and N-[11C]methyl catecholamines.

UR - https://www.scopus.com/pages/publications/0027371789

U2 - 10.1016/0969-8051(93)90094-B

DO - 10.1016/0969-8051(93)90094-B

M3 - Article

C2 - 8298573

AN - SCOPUS:0027371789

SN - 0969-8051

VL - 20

SP - 939

EP - 944

JO - Nuclear Medicine and Biology

JF - Nuclear Medicine and Biology

IS - 8

ER -

High yield synthesis of high specific activity R-(-)-[¹¹C]epinephrine for routine PET studies in humans

Abstract

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